A new bifunctional chain transfer agent (CTA) containing alkyne end groups was designed, synthesized, and used for direct synthesis of clickable telechelic polymers. Good control of reversible addition fragmentation chain transfer (RAFT) polymerization of N-(2-hydroxypropyl)methacrylamide (HPMA) was achieved by using the new CTA, as indicated by a linear increase of number-average molecular weight (Me) with conversion and low polydispersity (PDI) (<1.1). In particular, enzymatically degradable multiblock HPMA polymers were readily prepared by subsequent reaction with alpha,omega-diazido-oligopeptide (GFLG) sequence via Cu-I-catalyzed alkyne azide cycloaddition. Upon exposure of high molecular weight fractions of multiblock polyHPMA to papain or cathepsin B, the polymer was degraded into segments of molecular weight and narrow polydispersity similar to those of the initial telechelic polyHPMA.